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So, uh, I doubt Dio would take Tanjirou all that seriously. A young looking teen who isn't even slightly swole is quiet far from what is normally threatening to him at this point.

Tanjirou on the other hand would spell that he isn't a human, and Dio is immensly similiar to what a demon is, so he likwly goes for beheading from the start.

I doubt Dio would be afraid of the blade too, as it lacks the whole Hamon sthich as far as he knows, so probably Tanjirou by bypassing Dio's regen without the latter knowinf he can, I guess.
 
The blade is on magical fire, and I don't remember Dio freezing people literally every time he was in contact with something the enemy holds.
 
Not sure which key Tanjirou this is, so to be safe I'll say Post-Training.

Tanjirou via Enhanced Senses, Stats Amp, Info Analysis, and lastly Regen.
 
Part 3 DIO would be just bullying cuz in the manga and anime, Za Warudo's strength and speed are said to be similar to Star platinum and star platinum's strength can punch through stuff that is as hard as diamonds such as empress's teeth which was described as strong or even stronger than diamond, and the speed of star platinum was said to be faster than the speed of light which definitely stomps on reaction time, so he is practically invincible in demon slayer verse even without using time stop.
 
I'll vote Tanjirou, because he will first cut his arms, and then his neck, Killing in the process cause the nichirin sword will negate Dio Regenerationn.
 
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